the story goes he was semiforced out to go to rehab for gambling (see his first retirement announcement, not exactly sad, Phil looks pissed, stern is right there, etc..) not b/c of the literal gambling, but whom exactly he was gambling with. He literally had to testify at a federal drug and money laundering trial b/c he lost money gambling to a known felon and the IRS seized it...after he told the media AND authorities it was a loan to the guy (even worse haha)
http://articles.latimes.com/1992-10-28/sports/sp-858_1_jordan-claims
He then had 3 other checks, found in teh briefcase of a slain bail bondsmen FFS. totaling 108k. Then obviously came the businessmen that said he was owed 1.3M but only paid 600k (showed checks to prove it) and wrote a book about it
http://articles.latimes.com/1993-06-03/sports/sp-42795_1_san-diego
Then he was caught in Atlantic City in 93 at 0230 before a game, which the bulls lost the next day
http://www.nytimes.com/1993/05/27/sports/sports-of-the-times-jordan-s-atlantic-city-caper.html
the finally, during his retirement conference he said 'If David Stern lets me back in the league, maybe i'll come back'...
now faust brings up an excellent point regarding ownership, and i'm not saying i agree w/ the CT. But if say he never gambled on hoops, and then baseball counted as 'rehab' or a 'suspension'...then it would make sense to let him back in and later become owner. While he still gambled, i don't think he ever got into remote further legal issues over it